1,3-Dimethylimidazolium hexafluorophosphate
[CAS# 243664-15-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 1,3-Dimethylimidazolium hexafluorophosphate
• Molecular Formula: C₅H₉N₂.PF₆
• Molecular Weight: 242.10
• CAS Registry Number: 243664-15-5
• SMILES: CN1C=C[N+](=C1)C.F[P-](F)(F)(F)(F)F

Properties

• Melting point: 130 °C^*

^* Reichert, W. Matthew

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

1,3-Dimethylimidazolium hexafluorophosphate (also known as [DMIM][PF₆]) is a well-known ionic liquid with the molecular formula C₇H₁₀F₆N₂P. This compound is well known for its unique properties and has a wide range of applications in scientific research and industrial processes.

1,3-Dimethylimidazolium hexafluorophosphate was born out of research in the late 20th century that focused on developing ionic liquids with desirable properties such as low volatility, high thermal stability, and good ionic conductivity. The synthesis of this compound was part of a broad effort to create ionic liquids for specific applications in chemistry and materials science. The combination of the 1,3-dimethylimidazolium cation and the hexafluorophosphate anion produces a stable, highly conductive ionic liquid with a range of unique properties.

The synthesis of 1,3-dimethylimidazolium hexafluorophosphate generally involves the reaction of 1,3-dimethylimidazolium with an appropriate methylating agent to synthesize the cation. The hexafluorophosphate anion is generated by the reaction of phosphorus pentafluoride with other reagents to form PF₆⁻. Cations and anions combine in solution to form an ionic liquid, which is then purified and crystallized. The process produces a colorless, hygroscopic liquid with high stability and electrical conductivity.

1,3-Dimethylimidazolium hexafluorophosphate is widely used as an electrolyte in electrochemical devices such as batteries, supercapacitors, and fuel cells. Its high ionic conductivity and thermal stability make it ideal for these applications, improving performance and reliability.

In catalytic processes, [DMIM][PF₆] is used as a solvent and co-catalyst. It increases reaction rates and yields by providing a stable reaction medium and reducing side reactions. This application is valuable in organic synthesis and industrial chemical processes.

As a green solvent, 1,3-Dimethylimidazolium hexafluorophosphate contributes to sustainable chemical practices. Its low volatility and reusability reduce environmental impact compared to traditional solvents. It is used in a variety of green chemistry applications, including extraction and purification processes.

In materials science, this ionic liquid is used to synthesize advanced materials such as polymers and nanoparticles. It affects the properties of these materials, contributing to innovations in electronics, coatings, and other high-tech applications.

In analytical chemistry, [DMIM][PF₆] is used as a medium for various analytical techniques. It can be used as a solvent for extracting and analyzing compounds, improving the precision and accuracy of analytical methods.

References

2017. One-Pot Green Regioselesctive Synthesis of γ-Lactones from Epoxides and Ketene Silyl Acetals Using 1,3-Dimethylimidazolium Fluoride as a Recoverable Metal-Free Catalyst. *Molecules*, 22(9).
DOI: 10.3390/molecules22091385

2015. Experimental investigation of ionic liquid pretreatment of sugarcane bagasse with 1,3-dimethylimadazolium dimethyl phosphate. *Bioresource Technology*, 185.
DOI: 10.1016/j.biortech.2015.02.085

2022. Thermolytic Decomposition of Imidazolium Hexafluorophosphates. *Science of Synthesis*.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-142-00258